Finding Gayle by voloci2
Summary:

After moving back from the big city, Gale visits a small salon on a recommendation from a friend. The stylist, Theo, takes him on a journey that may change him forever.


Categories: Fiction Characters: None
Age Group: Adult 26-55
Categories: Crossdressing/TV
Genre: Fantasy
Keywords: Hair or Hair Salon
Story Universe: None
Challenges: None
Series: None
Chapters: 1 Completed: No Word count: 4029 Read: 6616 Published: 23 Jan 2016 Updated: 21 Feb 2016

1. Part 1 - The Special Package by voloci2

Part 1 - The Special Package by voloci2
Book

Part 1 “ The Special Package

The bell over the door to the old barbershop tinkled as I pushed it open and entered. It was only about five minutes before closing time and the old barber was sweeping up the day’s work into an old, battered trash bin. He didn’t look up at the sound of the bell, so I cleared my throat and raised my voice a bit, assuming he was hard of hearing, “I’m here to see … um,” I looked down at the scribbled note in my right hand, “Theodoros.”

Still without looking up from his work, the old man called out something in a language that I did not understand, but I thought I’d caught the name Theo at the beginning. After several seconds a much younger man emerged from the back room and made his way toward me at the front of the old store.

“Hello sir, I am Theo,” he said with a bit of an accent, extending his hand and shaking mine firmly. He was a well-built man who couldn’t have been older than mid-thirties. He wore a tight, white t-shirt and black slacks and his shiny black hair was pulled up into a ponytail.

“Uh, hi, my name’s Gale,” I said. “My friend Tony recommended that I come see you. I just moved back here and I’ve been looking for a barber that knows how to take care of long hair.” My own dark blonde hair reached below my shoulder blades when I left it down, but I usually wore it in a ponytail like today. Tony and I had been friends since grade school. One year in high school, we’d decided to grow our hair long to kind of rebel a little bit and we had both kept it long since then. What no one ever told us was that long hair wasn’t that easy to take care of, and, especially as guys, you had to find the right person to help you out.

“Ah, yes, Tony. How is he?” inquired Theo. I said he was doing fine in a tone that I hoped indicated that I wasn’t much for small talk. Theo seemed to understand as he stepped over to the front counter and asked, “What we can do for you today? Trim?”

“Well,” I responded, a little hesitantly, “Tony said that I should ask you about your special package.”

“Oh, yes,” said Theo as his eyes lit up and a smile crept across his face. “How much Tony tell you about it?”

“Not much,” I said, “just that it was a little expensive, but very well worth it.”

“Tony is right. I tell you what, I give you first time special. Only fifty dollars, what you think?”

I chuckled a little before replying, “I’ve been living in New York, fifty bucks has been the going rate for a haircut for a while. Sounds good to me.”

“Ok,” he said, “for special package we go upstairs, you are not in a hurry?”

“No, Tony said it would take a couple hours, so I cleared my schedule.”

“Excellent,” he said, smiling broadly again. “This way please.”

We mounted the stairs that exited off the side of the small shop and emerged in a fancy, single-seat salon. As much as downstairs was a run-down old barbershop, this room was state-of-the-art, glistening, clean and well-appointed. As I looked around I noticed that the salon seemed ready for any situation that it was presented with. There was a full shampoo station separate from the barber chair, as well as a hood dryer in one corner. There were all manner of scissors, clippers, and combs in one area, while another counter held perm rods and a variety of different chemical solutions.

“Let’s start with deep condition,” said Theo. For some reason, his accent and the funny way he phrased things really helped to put me at ease and made me feel more comfortable than I usually do the first time I’m trying out a new barber. He led me over to the shampoo station and made sure the water was well-warmed before he leaned me back. He definitely seemed to know what he was doing as his strong fingers massaged the shampoo into my scalp. It was one of the best shampoos I’ve ever had, and I was a little disappointed as he turned off the water and patted the extra moisture off with a towel.

Theo then applied the deep conditioner to my hair and combed it through before twisting my hair up on top of my head and moving me to the hood dryer. I quite enjoyed the heat of the dryer on me as Theo took a few minutes to arrange a few things over by the barber chair. Once the conditioning treatment was done, he rinsed me out again before sitting me down in front of the mirror and combing out my damp hair.

“You want to shave the face?” asked Theo as pumped me up a little taller in the chair.

“Sure,” I replied, figuring this must be a part of that special package.

Theo pulled out a straight razor and strop and proceeded to give me the closest, smoothest shave of my life. I couldn’t help starting to feel like this was going to be well worth the fifty dollars. But this was still a new place that I was trying out, so I couldn’t let myself get too relaxed.

Theo seemed to study me for a minute in the mirror from each angle. I really couldn’t tell what he was thinking so I was about to tell him that I just needed a trim when he completely threw me for a loop. “You have beautiful features,” he said as he pulled my hair behind my ears. “You ever try the cross-dressing?”

My face turned fire-engine red as I stammered out a reply. “N…no, no, not at all,” I said.

“Your face tells me a different answer,” said Theo. “You sure you never put on panties or a nice dress?”

“Well, no actually,” I said, “but I guess I’d be lying if I said I’d never thought about it. I think one of the reasons that I’ve kept my hair long for the last ten years is because I feel more feminine. But I’ve never told that to anyone before.”

“How ‘bout we let you have a little fun, no?” Theo said. He began to cross the room toward a door in the back and motioned for me to follow. I stood up and followed, confused at what was happening, but also curious and just a little aroused. Theo opened the door to reveal a large walk-in closet of various clothes and accessories, mostly women’s.

“I’m starting to see why Tony never explained about this special package.” I said, not realizing that I’d said it out loud.

“Tony doesn’t do the cross-dressing,” said Theo, “he’s too ugly.”

I chuckled at this, again feeling more at ease than I should.

“You don’t have to if you don’t want to,” said Theo, looking at me for an answer.

“No … I… I think I want to,” I said, not exactly sure what had come over me.

“Excellent,” was all Theo said before crossing the closet to another door which he opened and shouted something through. I looked around me at all the different clothing options available. There were lots of dresses, shoes, and other accessories, but also some pretty frightening looking BDSM getups as well. I hoped I got to choose for myself what I would put on.

Just then a squat, gray-haired old lady burst through the door. “This is Marina,” said Theo, “she will help you. See you in a minute.” He smiled and exited back into the salon.

Marina looked me up and down for a moment before half-shouting, “take off you clothes!”

“Excuse me,” I replied somewhat taken aback.

Once again she simply said, “take off you clothes!” before turning and disappearing down a row of the closet. I quickly stripped down to my briefs before she returned, but she took a quick glance at me, pointed at my underwear and cried again, “take off you clothes!”

As she went back into the closet, I stripped out of my briefs and asked myself how stupid I must be to be standing here stark naked in a strange closet with a strange old woman and to have paid $50 for the privilege. Before I could think anything else, Marina returned with a bra and breast forms and some tape. She began to tape the breast forms to my chest, adjusting them every now and again to get just the right shape. She then slid the bra over my arms and spun me around to clasp it in the back.

Marina stepped back and gave my new breasts a look of what I could only assume was approval before she indicated the entire closet and said, “Choose!”

“Don’t I get panties or something?” I asked, indicating my still nude pubic region.

“No,” she yelled again, “you no need … choose!”

I immediately eyed a bright-yellow sun dress that had caught my attention as soon as I’d walked into the closet. I was pretty slim and I wasn’t too tall, it looked like it might fit. I walked over and took the dress down off the rack. Marina nodded approvingly, grabbed the dress from me and pulled it off the hanger. She bustled about the closet for a minute until she returned with a pair of white pumps that I was pretty sure I’d never be able to walk in as well as a strand of (what I could only assume were fake) pearls, clip-on pearl earrings and a pearl bracelet.

She placed all the items into my outstretched arms, opened the door and ushered me back into the salon, exiting back into the closet and shutting the door behind her.

The first thing I noticed when I looked up was Theo, standing in the center of the room, obviously awaiting my arrival. I let out a little gasp as I saw him standing there, almost posing, completely and utterly nude. He was certainly well muscled and toned and his skin had that nice Mediterranean glow. He wasn’t overly hairy, though what he had was dark, and he had manicured his pubic hair into an attractive little triangle. But definitely what stood out the most was the thing that stood out. His cock was enormous. Besides just being well endowed, his penis was the perfect shape, the absolute epitome of manhood, he probably made porn stars jealous. Next to this Adonis, I’m sure I looked like a scrawny little teenager, with fake boobs on, of course.

I’m sure the shock was evident on my face as he smiled that dashing smile once again. He motioned for me to put down the things that I had brought from the closet and said, “c’mon, we shave.”

Something about this whole situation was making me very submissive. As I look back on it, I can’t believe that I was as obedient and open as this with a person who was still, at the time, a perfect stranger.

Theo must have been satisfied that I didn’t have much chest hair to deal with, since he didn’t remove the bra or breast forms. He carefully worked around them to remove the sparse hairs that would show from out of the scooped neck of the sundress. Next he sat me up on a towel covered table that he had positioned in the center of the room and started, working from my ankles up, to shave my legs. “You have nice legs,” he said approvingly, “toned, firm, not too thick.”

“Um, thanks,” I said, quite embarrassed at this point. But despite my embarrassment it was obvious to me, and of course to Theo as well, that I was enjoying this treatment. My thin pole stood at attention, hardening a little more with each stroke of the razor. When he finished my right leg, I realized he was right. I did have really nice legs. I liked to run and I’m sure this helped keep them in shape, but they weren’t overly muscular. Without the hair, they looked quite feminine and attractive.

He kept me on the table as he retrieved a small, battery operated trimmer from a drawer. I must have been lost in the experience since I absolutely did not expect what came next. Theo took hold of my penis with one strong hand and plunged the trimmer into my pubic hair with the other. He was relentless with the trimmer, raining pubes on the towel beneath me as he buzzed all around my crotch, pole and balls. It was at this point I realized that I was genuinely getting turned on. I realized how handsome Theo was, how his firm hold made me feel completely under his control. I’d never been with another guy before. I’d thought about it a little. I even made a list of celebrities that I’d be willing to go down on, but I never thought of it as more than a little playing around. I liked women. I loved pussies. This attraction to Theo was different, but not unnerving, as if I was being provided with a no-strings-attached opportunity to try something new.

Without a word he spread shaving cream all around the area that he had just buzzed. With each stroke of the razor I let out a soft moan, trying to give a little indication that this was working for me. I thought I saw a sly smile spread across Theo’s face at the sound of my pleasure.

“Ok, now we turn over. On hands and knees please,” he said as he rinsed out the safety razor fresh from denuding (what was left of) my manhood. “Now we going to shave your ass,” he said, more delight and eagerness in his voice than I had heard before. He was obviously quite good at this, as throughout the whole experience I never got a single nick or scrape. As he was wiping the shaving cream from my ass, he seemed to be paying extra attention to my anus. When he began rimming it with the tip of his finger, chills went up and down my spine and I started moaning again.

“You like this?” he asked.

“Mmm hmm,” was all I could get out, the ability to form words having escaped me.

“You have ever take it in the ass before?” he asked. This question should have shocked me, but feeling the way I was at that moment, all I could do was squeak out a little sound approximating the word no. On hearing this, Theo drove his finger into my asshole. The initial feeling was intense pain as my anus opened up to accommodate the foreign object, but it didn’t last as incredible pleasure set in. He worked his finger in and out for several minutes and I began to writhe in ecstasy. I exploded all over the towel at the moment that he removed his finger and inserted his tongue into my hole.

After my body relaxed I began to feel embarrassed again about what had happened when Theo said, “You no worry. It gets better.”

I cleaned myself up as Theo wiped off and put away the table. He had me douche to clean myself out (it wasn’t nearly as gross as I thought it would be) which led me to believe that we weren’t done with that experimentation yet. I also put on the dress and the heels, though I didn’t wear the jewelry quite yet. Theo sat me down in the chair and twisted my hair up on the top of my head. He then swooped around in front of me with a small tray of make-up. This guy could do everything! He put on foundation, mascara, eye liner and shadow (a nice light blue), blush, and lipstick (baby pink) and then moved out of the way so I could look in the mirror.

I was absolutely floored! I looked great. I could pick out bits and pieces of my look that were still a little masculine, but overall it was a very pretty look. Heck, after a couple of drinks I’d probably tap me. Theo then opened a bottle of pink nail polish which was pretty close to the color of my lips and painted each of my nails in turn, fingers and toes.

“Now, for the reason you came,” Theo said, letting my hair down from the clip that was holding it up. “We do a little trim and maybe some long layers,” he added combing through my hair. I was in no mood to argue since I was really enjoying watching in the mirror. I watched as he finished combing my hair and picked up the scissors and started to take about a half-inch off of the length off my hair. He was very methodical, with great attention to detail. It was cute how he bit his bottom lip a little bit as he made each cut. Soon he was lifting my hair, adding layers throughout the length. Every now and then I’d catch his deep brown eyes looking at me in the mirror, and I have to admit, it made me feel a little shy.

“Do you want perm or set?” Theo asked, snapping me out of an imaginative trance.

“Um, isn’t a perm, you know, permanent?” I asked.

“It would last a few months. If you don’t want that we do a set, it will wash out.”

“Yes, let’s do a set,” I said, not ready or willing to commit to this kind of role-play full time.

“Very good,” Theo responded. He busied himself gathering all of the necessary tools to ply his trade. Before I knew it he was combing a thin lotion through my hair. Next he began to roll my freshly trimmed hair around one-and-a-half inch rollers and pin them in place. Once all of the rollers were in, he covered my head with a loose hair net and sat me under the dryer.

“So what do you think?” asked Theo. “Is this worth the fifty dollar special?”

“You tell me,” I winked at him and pointed to my erect pole making a little tent out of the pretty yellow dress I had on.

“Thank you for the invitation,” he said, smiling. He knelt down in front of me and lifted the sundress off of my lap. My tiny little cock, even when fully erect, didn’t seem as long as his huge masculine penis was even at rest. Theo softly caressed my newly bald crotch and gently fingered my balls as he ran his strong, firm tongue over every inch of my newly-bald pubic area. I then experienced the wonderful sensation of Theo bringing his strong pursed lips down around my dick, gliding up and down and sucking rhythmically to heighten the sensation.

Just as I could feel climax coming on, the timer on the dryer buzzed, indicating that I was done. To my great disappointment, Theo jumped up immediately and helped me out of the dryer chair and back into the salon chair. He slowly unwound each roller and I watched, mesmerized, as each wave of curly goodness fell from the roller and onto my shoulders. Theo tenderly arranged each curl and held it in place with what seemed like massive amounts of hairspray.

“Ah, that work very nice,” commented Theo as he fastened the necklace, and helped me put on the earrings and bracelet. After a few spritzes of perfume, he took me gently by the hand, stood me up and spun me around in front of the mirror. Looking back, I know I wasn’t a supermodel “ still a little too wide in the shoulders and narrow in the hips, too strong of a jaw, amongst other things - but I absolutely fell in love with the way I looked in the mirror.

Something I’d never felt before overcame me and I put my hands on either side of Theo’s face and kissed him hard, full on the mouth. The wonderful illusion of my femininity continued as he slipped his strong muscular tongue between my lips. He then turned, sat in the salon chair and pulled me down on top of him. As I straddled and continued to kiss him, I could feel his enormous phallus tickling my newly bare bum. After several minutes of making out, he pushed me back away from him and spread his legs wide. He grabbed me firmly by the back of my head and pushed my face down toward his glistening, well-toned crotch. I opened my mouth wide and nearly gagged as he thrust his dick deep into my throat. I began to move my head up and down, taking his manhood into my mouth and firmly squeezing it between my lips as I pulled off. The feeling of that tremendous specimen of meat in my mouth was exhilarating. It was so firm and erect and, I didn’t know if this was one of Theo’s special tricks or not, but it tasted exquisite.

After what seemed like ages I got a little exasperated that I couldn’t make him cum, no matter how hard I tried. As I sat up, panting, Theo said, “you no worry, I only cum for real woman. After a while, I cum for you. It is worth the wait.” I didn’t have time to process his comment though, since he hurriedly traded places with me and fully reclined the salon chair in which I now sat. This time he straddled me and began kissing me again as passionately as I can ever remember being kissed. Impressively, as he balanced on the edges of the salon chair with his knees and continued to kiss me, he lifted my smooth, sexy legs up onto the armrests of the chair and began caressing them with his well-toned, muscular hands and arms.

Suddenly, a shockwave of painful ecstasy ripped through my body as he rocked back and thrust his cock into my unprepared asshole. I didn’t know if my scream was from the pain of having his huge member stretch me out or the indescribably joy of having someone inside of me. As Theo moved back and forth, in and out, I realized that I wasn’t going to be able to go back to being the penetrator. This singular experience was either going to ruin sex for me forever, or make it the most wonderful, transcendent experience ever.

It didn’t take long for me to ejaculate for the second time in the last hour. I don’t think I’d ever cum twice that close together before. Theo stood up and smiled his handsome smile once again. “That completes our special package,” he said. “If you want to keep clothes, jewelry, and all you can pay, or you can make another appointment at regular price.”

“I’d like to make another appointment,” I said quickly, trying to imagine how I could ever go anywhere else after this.

“Ok, but only one special package for every four weeks, so we do next month.”

“Great,” I blurted out, wondering if I could wait a whole month for my next appointment. We got scheduling squared away and Theo kissed me goodbye on the cheek. I walked out to my car in the pretty yellow sundress with my boy clothes in a bag and I didn’t even give it a second thought. I didn’t know what the end result of all of this was going to be, but I knew that night had changed me forever.

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